JEE Main Chemistry question

ChemistryAlcohols, Phenols and EthersJEE Main

How many of the following ethers CANNOT be prepared by Williamson's synthesis? , (diphenyl ether), , , (di-tert-butyl ether).

Answer: 2

Solution

Williamson's synthesis requires a primary (unhindered) alkyl halide reacting with an alkoxide; it fails when the alkyl halide required would be an aryl halide (which cannot undergo the needed nucleophilic substitution, as in

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Question ID VK-149031